(2R,3R,4S,5S,6R)-2-((R)-4-(2,4-dihydroxyphenyl)butan-2-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

ID: ALA3100132

PubChem CID: 71769044

Max Phase: Preclinical

Molecular Formula: C16H24O8

Molecular Weight: 344.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](CCc1ccc(O)cc1O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C16H24O8/c1-8(2-3-9-4-5-10(18)6-11(9)19)23-16-15(22)14(21)13(20)12(7-17)24-16/h4-6,8,12-22H,2-3,7H2,1H3/t8-,12-,13-,14+,15-,16-/m1/s1

Standard InChI Key:  XNCMTBXGJAVONM-XIXKKTEDSA-N

Molfile:  

     RDKit          2D

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   13.7277   -5.9261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0124   -6.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0022   -7.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7066   -7.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4226   -7.1572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4293   -6.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1268   -7.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1199   -8.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8241   -8.8036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8172   -9.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5353   -8.4010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3101   -5.9084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2395   -8.8156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2279   -9.6357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9281  -10.0502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6416   -9.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6505   -8.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9459   -8.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2353   -7.9944    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.9539   -7.5968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3442  -10.0684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3630   -8.4329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9180  -10.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2054  -11.2672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1407   -5.9389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  6
  2 12  1  0
 11 13  1  0
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 13 19  1  6
 18 20  1  6
 16 21  1  6
 17 22  1  1
 15 23  1  1
 23 24  1  0
  6 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3100132

   (2R,3R,4S,5S,6R)-2-[(2R)-4-(2,4-dihydroxyphenyl)butan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 344.36

Molecular Weight (Monoisotopic): 344.1471

AlogP: -0.76

#Rotatable Bonds: 6

Polar Surface Area: 139.84

Molecular Species: NEUTRAL

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.54

CX Basic pKa: ┄

CX LogP: -0.02

CX LogD: -0.03

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.40

Np Likeness Score: 1.90

References

1. Iwadate T, Kashiwakura Y, Masuoka N, Yamada Y, Nihei K..  (2014)  Chemical synthesis and tyrosinase inhibitory activity of rhododendrol glycosides.,  24  (1): [PMID:24332496] [10.1016/j.bmcl.2013.11.063]

2. Iwadate T, Nihei K..  (2015)  Rhododendrol glycosides as stereospecific tyrosinase inhibitors.,  23  (20): [PMID:26386819] [10.1016/j.bmc.2015.09.014]

Source

Source(1):

• Scientific Literature